Hardest Relative NPC

And all three are pretty bad in the long term, and Pelipper is best used as a HM slave.

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Last two times I went against norman I brought in a Dustox I had evolved way earlier and toxistalled his Slaking(s)
it was pretty great

Never used the Dustox again but it's my go-to guy if I don't want to mess with that monster. Not like it takes much time to set it up, either.

edit: Oh saw the mention of all the HP compared to Protect's limited PP
Don't forget you have the Truant turns (and depending on how the match has gone, the heal up turn where you can put down toxic if you wanted) where you don't have to protect. Deal (pitiful) damage, inflict Confusion whatever. All that little damage adds up with Toxic.
Chances are it'll be dead before turn 20

Generally I try to feed as much EXP into the main Pokemon as possible, but Dustox is probably one of the most reliable ways of beating the bastard. If only it was actually useful for anything else after Norman :<

Orange Islands

Not understanding Bronzong's typing can really bone you in that match. My first E4 attempt I got all the way to his Bronzong which went on to totally curbstomp me. I just couldn't work it out at all, it was so defensive. It can catch off guard if you have no idea what is coming.

Not understanding Bronzong's typing can really bone you in that match. My first E4 attempt I got all the way to his Bronzong which went on to totally curbstomp me. I just couldn't work it out at all, it was so defensive. It can catch off guard if you have no idea what is coming.

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Considering the endless masses of Bronzor you have to sit through to even get your way to Lucian I'd say you should already have a good idea of what's Bronzong's typing

When I was little I always had trouble with kingdra in GSC. I thought ice types would work. You couldn't even have a dragon move by then, well gyarados with twister and I think dratini from the game corner in Goldenrod.

Gen 1
RBY: Misty, everyone has already mentioned why. Now whenever I do a R/B run I make sure to have gyara. Honorable mentions goes to Lance in Yellow, Dragonite hits like a locomotive.

Stadium: Lance, amnesia snorlax that explodes, great. Plus he loves to spam wrap/fire spin. Ugh. Agatha, gengar and zam on the same team. Jynx and Gyara too, the fight can be hellish.

Gen 2
G/S/C: Meh, whitey isn't that hard. More annoying than anything. I'd have to say Red and only because your levels probably don't come anywhere near his.

Stadium 2: Fuck little cup.

Gen 3
R/S/E: Liza and Tate, I just never seem to be prepare for that one. Claydol needs to die quickly too because it just spams EQ all day. Honorable mention to Brawly and the rival battle above slateport. Swampert trolls the rest of the game.

FR/LG: the Rocket who is trying to get the random gem thing from the scientist. I don't even remember why this fight is hard. just that it is.

Colloseum: Nascour and Evice. Not ready for that battle, even with tower grinding beforehand and their shadows are HARD to catch. Succeeding in catching them doesn't make the fights any easier either. Honorable mention to Miror B, fuck rain dance

XD: The moron with the Shadow Zangoose. You access him early, I did so by mistake, and got obliterated by that thing. Honorable mention to Gorigan for EQ spamming when I have no flying types.

Gen 4
D/P/Pt: Cythina, hands down. She just doesn't have any really exploitable weak points on her team and garchomp is by far the most dangerous thing you have encountered up to that point. I had a team of Garchomp/Gastrodon/Infernape/Bronzong/Roserade + HM slave (Level 55-57) and still had trouble. With SR in play. Honorable mention to Crasher Wake, unless you have a grass type, then he dies.

HG/SS: Doing a play through right now and nothing has really jumped out at me. (Dragonair/Meganuim/Togetic/Quasire Level 39-40 about to fight clair) Gonna have to say Lance rematch since spamming an ice type isn't an auto win anymore. Honorable mention to Red for the level 88 Light Ball Pikachu and hail+blizzard spam.

Gen 5
B/W: This is a joke right? I abandoned my team and starter in favor of some of the newer pokes half way through and still completely overran the E4 and Ghetsis. The lucky egg means I don't have to bother grinding anymore. Post game I can immediately catch a level 50 Dratini that has both DD and Outrage?! Yea, piece of cake.

B2/W2:
Normal mode: I swept the ENTIRE elite 4 with Zoroark. Including the champ and marshal. Genosect before the 1st gym. Well, that will learn me for using event pokes in game.
Challenge mode: This is more like it, but still too easy. Especially compared to the earlier games. Part of the problem is that you can assemble a pretty good team very early. Luke, maggy, Arcanine, starter/haxourus, two slots for w/e. Honorable mention goes to the post game battles of Colress, Benga, N and Cynthia. Although Cynthia is somewhat of a letdown compared to what she was in gen 4.

Really? You were having trouble with Zook in XD? (That's the shadow zangoose guy, I'm actually doing a random run-through of if right now when I'm bored). I find him really easy, the person I always have trouble with, every run-through is Snattle in Phenac city. Seriously!? I mean, there are 2 super-effective pokemon with the only super-effective type on his Quagsire. There is only 1 super-effective on Lanturn, numel, who would get OHKO'd by it. 4 super-effective on metang, one of them being numel again. And only 1 again on Castform: Makuhita... That is just sad. Not to mention all of his pokemon have great defense stats, but most of them solely have attacking moves, meaning that they sweep, and you can't sweep them. Not to mention after shadow sky from Lunatone, Castform gets a shdow type weather ball, which sweeps like hell. I remember on my first run-through of XD, it literally took about a day and a half to beat him, and though I got better on my long stream of plays, I have never beaten him within 3 tries. He is absolutely OP...

Route 18 is absolutely brutal in B2. First there's that veteran lady with the kingdra triple battle. That was the first time i realized dragon Pulse can hit all sides. Then theres the guy with the lv. 70 Tyranitar. And finally, the lady with the lv 70 Salamence. Those fights were disgustingly hard. And of course, Colress is lying in wait there.

Crasher Wake, hard on Platinum? I don't think so, I defeated him at the first try with my usual underlevel team (I never grind) at level 22-26 (against him's team of level 33-37), and... that was really easy, Pachirisu (lv26) can take, outspeed and destroy him's Gyarados every day with a simple spark, Quagsire is just unnable to resist any grass attack, and even without them, he's even unnable to take repeated special attacks from whatever thing, and Buizel can strike hard, but he have thin paper defenses, so... almost any Pokémon who can resist a single attack can beat him in 1-2 turns, and the list of somewhat resistant Pokémon at the moment is whatever thing less low. You can also just use charm on it and change to whatever thing resistant to Brine, again, Pachirisu can easy do that without any major trouble, and even whatever Pokémon with charm.

I had trouble with Wattson on my Christian playthrough of Emerald, since I couldn't evolve Mudkip. I eventually gave up and spent half an hour looking for a Geodude.

There's also that person in Pokemon Diamond with the Bronzor near Cycling Road. That thing completely shut my team down with Hypnosis and Imprison. I've never had that much trouble with anything before.

Wattson made me hate emerald for so long. My battles against his magneton were parahax everywhere. I eventually got so fed up with it I went back to that cave near dewford, caught a sabeleye and powerleveled it to level 35 so its nightshade was enough to beat Wattson.

Route 18 is absolutely brutal in B2. First there's that veteran lady with the kingdra triple battle. That was the first time i realized dragon Pulse can hit all sides. Then theres the guy with the lv. 70 Tyranitar. And finally, the lady with the lv 70 Salamence. Those fights were disgustingly hard. And of course, Colress is lying in wait there.

Wattson made me hate emerald for so long. My battles against his magneton were parahax everywhere. I eventually got so fed up with it I went back to that cave near dewford, caught a sabeleye and powerleveled it to level 35 so its nightshade was enough to beat Wattson.

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shedinja is a great choice for emerald wattson, only weak to voltorb's rollout (of which if you're lucky he might boom instead) and magneton's supersonic.

That one veteran with a Sigilyph in BW2 Victory Road (Veteran Cathy, apparently). Think you can just take it out easy with a weakness? NOPE, hypnosis then slaughter. To be fair I think I was 3 or 4 levels below it but still.

Obvious 4th gen Cynthia (I don't recall a single instance I faced her without spamming revives, some to the point of PP stalling vital moves)

Had some trouble on Mars's Purugly (round 1) and the HGSS Kimono girls as well (The latter is pretty much the cause of my only whiteout in Soul Silver)

Misty in LG gave me trouble because of hax and my team being Mankey lvl22 and Charmeleon at 24, plus I had to rely on inaccurate moves to beat her(mega kick and punch, rock tomb). I had to go below Cerulean and catch a bellsprout with sleep powder to finally beat her and I still was only barely able to beat her.

He's been mentioned. No need. I didn't find him overly difficult though, maybe my teams just bawz! ¬_¬
Almost every pokemon has a downfall:
Rain:
Politoed's hypnosis misses too much generally giving a free turn.
Lanturn has stockpile. Fail. It might raise defenses, but it doesn't hurt that much. I have 1 OHKO moves on my team which makes it redundant, and spamming it just lets you whittle down the health which he has done in the past.
Tentacruel can't hit a multitude of types. Dragon (but lot's don't.). Ice (somehow). And it seems very interested on keeping it's defenses high with barrier, occasionally letting burn takes it toll and if the hax is good then paralyze as well. Besides, hydro pump being the only strong move any type that resists water is pretty much fine, since giga drain really doesn't hit hard at all.
Omastar doesn't really have one.
Kabutops has low kick. Low kick It's wrong on so many levels I'm not going to explain it to you.
Starmie is great, but can be taken down fairly easily.

Sun:
Ninetails has confuse ray and foul play. Confusion can be annoying. Oh god. Foul play... well.. Don't use a pokemon with a high attack! :P Also life orb is rubbish on it. Foul play doesn't get boosted by the item (I think, I don't use it in play but I'm pretty sure it's right) and for such a fragile pokemon without a recovery it truly is terrible.
Arcanine is great, however if you play well you can come in and hurt it while it is locked into outrage. Or get lucky with confusion hax.
Rapidash has a random special move. It has good coverage, I suppose, but drill run is too weak being neutral, flare blitz recoil can be fatal for a fragile pokemon like rapidash and the only good move is megahorn. Megahorn is great on a number of levels, the rest are not.
Shiftry... Man. Did this guy give some amount of trouble. Focus miss misses a lot though, but that's pretty much it.
Ninjask is random, has solar beam on a low special attack, 1 physical attacking move, which is X-scissor, and has protect, which is for speed boost. However, the point of protect speed boost is to use it for a free speed boost when he is sent out, but sometimes he uses it 2 or 3 turns into the battle and while annoying does nothing for it. It can not touch flying types, or lots of pokemon that resist bug (which is a lot) since solar beam won't hit hard enough even on rocks to KO it anyway (except rock/ground and some rocks like onyx).
Leafeon has attract. Damn. ANOTHER X-scissor puts 3 bug moves on his team for no reason, and particularly for leafeon it could be used for something far better. iron tail is generally bad, but at least he has leaf blade.

Not to mention even his sand and hail teams. Come on, a Hippowdon with Superpower instead of Earthquake? And no Sand Rush Excadrill? Props for Scizor, though. As for hail, what's up with Cloyster? I was assuming your standard Shell Smash-Skill Link fare. But it isn't exactly that set. In fact there's no focus sash. But if there were a sash on the hail team, then where else would sashes go? Ninjask? Perhaps a Shell Smasher on the rain team? Come to think of it, leftovers as well. Good on every lead except Abomasnow. At least Life Orb is good on that guy.

I was thinking.. and Bugsy! Every single play-through of the game I have played it has required me to grind at least 2 or 3 levels, which wouldn't be bad except that you're at level 16 grinding on level 4s! But the giant level leap and minimal training agrivates you. And the fact that scyther pretty much gets at least 3 free hits on your pokemon, all 3 on U-turns. While scyther completely spams U-turn, it has base 70 in the second gym which is just completely OP, especially since it's a move that is often used in competitive battling!

Gold/Silver/Crystal: Metapod is just annoying and will PP waste you some turns, just use whatever thing who doesn't care about String Shot and the PP lose. Kakuna is almost the same, but you'll gonna have to waste maybe an antidote if he poison your Pokémon early, when Kakuna is almost defeated, change to your favorite bird/rock/electric Pokémon, or just to your Cyndaquil or Totodile (if you choosed Chikorita, just use the others types already mentioned), Scyther have great attack, but he doesn't have attacks to use it at all, he'll spam Fury Cutter until it reaches to unstopables levels... of course, this battle is actually easy if you have a Super Efective attack, or just a Pokémon who can handle him's first Fury Cutters and deal good neutral damage (Totodile), pretty straightfoward. If you don't have the correct types, you can still use an X-Attack and try to get rid of him with whatever neutral damage, him's Fury Cutter will not reach to usable levels until 3-4 turns, you have the time to set up and get rid of him, and even if he reachs to powerful levels of Fury Cutter, Onix can still wall him all the day (Geodude can, too, but he may have problems and you'll need more potions in that scenary).

Remakes: Now Metapod can't stall your PP. When Metapod is on the field, just set up whatever you want if you have a set up move or have the X-Items; if the answer to boths are nope: Then just get rid of the Metapod fast. Against Kakuna just have some Antidotes for the possible Poison, but now Kakuna can't stall your physical attacks without Harden, so, that's not too much probable, Zubat/Beedril/Gastly cannot even being poisoned, if you're having troubles of money.

Finally, Scyther, he's really excesive easy to beat, he's the same as before, but now have Sitrus Berry, changed Fury Cutter for U-Turn, and have Focus Energy, well, U-Turn is a lot easy to manage than Fury Cutter, actually, Fury Cutter can reach to 160 of power if you're not having the enough raw power to stop it before, but U-Turn can't just increse it's power, 70 + Stab is good, but any Pokémon with decent defense can resist 1 (or even 2) rounds and destroy him with any super effective attack. Geodude and specially Onix can wall him all the day and give him back a wonderful Rock Thrown (Scyther is x4 weak to it), Cyndaquil can resist 1 U-Turn and give him back Ember, Pidgeotto can resist him without any trouble at all (2 or even 3 hits) and just destroy him with whatever flying-type attack, Zubat can wall Syther all the day with him's x4 resistance to U-Turn and just ate him with Wing Attack (or Bite if you're low leveled). Even Gastly can resist 2-3 U-Turn with him's double resisntance and just Curse Him if Kakuna and Metapod are out from the battle, or just spam Night Shade.

Actually, Scyther is just a problem if you're not carring anything who can resist bugs attacks, or can give him back a super-effective. Fighthers, Fire, Flying, Ghost, Poison, (and steel) resist him's U-Turn. Fire, Flying, Electric, (Ice), and Rock (x4) can strike him back with super-effective. If you're not having any of those defensive or attack types, your team sucks as hell.